红树植物土壤微生物Streptomyces xiamenensis sp. nov.化学成分研究
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摘要
红树植物处于特殊生境中,具有独特的代谢方式,因此其代谢产物具有结构多样性和活性多样性。为了寻找其中结构新颖、有潜在活性的化合物,本论文对来自福建漳江口红树林保护区红树植物土壤微生物样品Streptomyces xiamenensis sp.nov(编号为318号菌株)进行了系统的化学成分研究。
本实验综合运用硅胶色谱,制备薄层(PTLC),凝胶柱色谱(Sephadex LH-20),反相柱色谱(ODS)和高效液相(HPLC)等色谱手段和波谱学技术,从培养基部位分离43个化合物,其中鉴定化合物37个,其次生代谢产物类型主要有单萜生物碱1个,吲哚生物碱7个,环二肽14个,含苯环小分子以及氮杂环类化合物15个,分别为：2-丁烯酸(1),苯乙酸(2),邻羟基苯甲酸(3),7-羟甲氧基吲哚(4),对羟基苯丁酮(5),对甲氧基苯甲酸(6),3-苯基-2-丙烯酸(7),环[亮氨酸-脯氨酸](8),环[L-苯丙氨酸-脯氨酸](9),次黄嘌呤(10),环[D-苯丙氨酸-脯氨酸](11),2-H嘌呤-2-yl,2-氨基酸-1,3,6,9-四氢化-6含氧-9-β-D呋核亚硝脲(12),对羟基苯甲酸(13),阿魏酸(14),(S)-2’,3’二羟基-3-吲哚丙酮(15),(R)-2’,3’二羟基-3-吲哚丙酮(16),苯并吡喃衍生物(17),2,4-二羟基苯甲酸(19),环[脯氨酸-缬氨酸](23),2’-甲基3-吲哚甲酸(24),对羟基苯甲酸甲酯(25),3-吡啶乙醇(26),甲酯-2-羟基-3-吲哚丙酸(27),环[甘氨酸-亮氨酸](28),N-苯乙基乙酰胺(29),环[亮氨酸-丙氨酸](30),环[缬氨酸-亮氨酸](31),环[酪氨酸-脯氨酸](32),环[丙氨酸-异亮氨酸](33),环[丙氨酸-缬氨酸](34),环[色氨酸-丙氨酸](35),环[色氨酸-丝氨酸](38),环[色氨酸-缬氨酸](39),对苯二酚(40),环[色氨酸-脯氨酸](41),2’-羟基-3-吲哚丁酮(42),吲哚甲酸(43)。各化合物均为首次从该种分离得到。
总结工作：第一,该微生物的次生代谢产物的量少,没有足够的样品量进入活性筛选；第二活性筛选的范围不够广。所以该工作还需进一步完善,发挥微生物可以扩大培养、而不破坏生态环境的优势,同时研究培养方法的优化,是次生代谢产物定向生成,进行高通量活性筛选,寻找新颖化合物的独特活性。
The metabolists of mangrove microorganism show diversities in structure and activity because of particularity in their living environment.In order to investigate the metabolists with novel structure and potential bioactivity,we have systematically investigated the chemical constituents of the microorganism Streptomyces xiamenensis sp.nov.,which was separated from mangrove soil in FuJian province.
On the basic of silica gel column chromatography,PTLC,Sephadex LH-20 column chromatography,ODS column chromatography,HPLC,fourty-three pure compounds were obtained from the mangrove soil microorganism,guided 1H-NMR spectrum and DAD-HPLC analysis.thirty-seven structures were determined spectroscopic analysis,including NMR,MS,IR,UV spectra,which are 2-Butenoic acid (1), Benzeneacetic acid (2), Benzoic acid (3),1 H-Indole-7-methanol (4),1-Butanone,1-(4-hydroxyphenyl) (5), Benzoic acid,4-methoxy-, hydrochloride (6),2-Propenoic acid,3-phenyl (7), Cyclo(leucyl-proline (8), Cyclo(L-Phe-Pro) (9),7-methyl-1H-purin-6(7H)-one (10), Cyclo(L-Phe-Pro) ( 11),2H-Purin-2-yl,2-amino-1,3,6,9-tetrahydro-6-oxo-9- -D-ribofuranosyl-(12),4-hydrox ybenzoic acid(13), Fumalic acid(14), (S)-2',3'-dihydroxy-1-(1H-indol-3-yl)propan-1-one(15 ), (R)-2',3'-dihydroxy-1-(1 H-indol-3-yl)propan-1-one(16), Benzopyran derivatives(17), 2,4-dihydroxybenzoic acid(19), cyclo[Pro-Val](23),2'-methyl-1H-indole-3-carboxylic acid(24), methyl 4-hydroxybenzoate(25),3-Pyridineethanol(26), methyl 2-hydroxy-3-(1H-indol-3-yl)propanoate(27), cyclo[Gly-Leu](28), N-phenethylacetamide(29), cyclo[Leu-Ala](30), cyclo[Val-Leu](31), cyclo[Tyr-Pro](32), cyclo[Ala-IIe](33), cyclo[Ala-Val](34), cyclo[Trp-Ala](35), cyclo[Trp-Ser](38), cyclo[Trp-Val](39),1,4-Benzenediol (40), cyclo[Trp-Pro](41),1-Butanone,2'-hydroxy-1-(1H-indol-3-yl)-(42),3H-Indole-3-carboxylic acid (43)。
In a word,there were two problem needing to resolved.Firstly,amount of the secondary metabolists that microorganism produced was very little,so it was difficult in screening.Secondly,the range of screening was so limited.In order to search special activities of novel compounds and provide guiding compounds for studies on new medicine, we should take better advantage of mangrove soil microorganism,such as enlarging fermentation scale,optimize culture method to produce secondary metabolists directionally and screen in highly efficient and wide-ranging way.
本实验综合运用硅胶色谱,制备薄层(PTLC),凝胶柱色谱(Sephadex LH-20),反相柱色谱(ODS)和高效液相(HPLC)等色谱手段和波谱学技术,从培养基部位分离43个化合物,其中鉴定化合物37个,其次生代谢产物类型主要有单萜生物碱1个,吲哚生物碱7个,环二肽14个,含苯环小分子以及氮杂环类化合物15个,分别为：2-丁烯酸(1),苯乙酸(2),邻羟基苯甲酸(3),7-羟甲氧基吲哚(4),对羟基苯丁酮(5),对甲氧基苯甲酸(6),3-苯基-2-丙烯酸(7),环[亮氨酸-脯氨酸](8),环[L-苯丙氨酸-脯氨酸](9),次黄嘌呤(10),环[D-苯丙氨酸-脯氨酸](11),2-H嘌呤-2-yl,2-氨基酸-1,3,6,9-四氢化-6含氧-9-β-D呋核亚硝脲(12),对羟基苯甲酸(13),阿魏酸(14),(S)-2’,3’二羟基-3-吲哚丙酮(15),(R)-2’,3’二羟基-3-吲哚丙酮(16),苯并吡喃衍生物(17),2,4-二羟基苯甲酸(19),环[脯氨酸-缬氨酸](23),2’-甲基3-吲哚甲酸(24),对羟基苯甲酸甲酯(25),3-吡啶乙醇(26),甲酯-2-羟基-3-吲哚丙酸(27),环[甘氨酸-亮氨酸](28),N-苯乙基乙酰胺(29),环[亮氨酸-丙氨酸](30),环[缬氨酸-亮氨酸](31),环[酪氨酸-脯氨酸](32),环[丙氨酸-异亮氨酸](33),环[丙氨酸-缬氨酸](34),环[色氨酸-丙氨酸](35),环[色氨酸-丝氨酸](38),环[色氨酸-缬氨酸](39),对苯二酚(40),环[色氨酸-脯氨酸](41),2’-羟基-3-吲哚丁酮(42),吲哚甲酸(43)。各化合物均为首次从该种分离得到。
总结工作：第一,该微生物的次生代谢产物的量少,没有足够的样品量进入活性筛选；第二活性筛选的范围不够广。所以该工作还需进一步完善,发挥微生物可以扩大培养、而不破坏生态环境的优势,同时研究培养方法的优化,是次生代谢产物定向生成,进行高通量活性筛选,寻找新颖化合物的独特活性。
The metabolists of mangrove microorganism show diversities in structure and activity because of particularity in their living environment.In order to investigate the metabolists with novel structure and potential bioactivity,we have systematically investigated the chemical constituents of the microorganism Streptomyces xiamenensis sp.nov.,which was separated from mangrove soil in FuJian province.
On the basic of silica gel column chromatography,PTLC,Sephadex LH-20 column chromatography,ODS column chromatography,HPLC,fourty-three pure compounds were obtained from the mangrove soil microorganism,guided 1H-NMR spectrum and DAD-HPLC analysis.thirty-seven structures were determined spectroscopic analysis,including NMR,MS,IR,UV spectra,which are 2-Butenoic acid (1), Benzeneacetic acid (2), Benzoic acid (3),1 H-Indole-7-methanol (4),1-Butanone,1-(4-hydroxyphenyl) (5), Benzoic acid,4-methoxy-, hydrochloride (6),2-Propenoic acid,3-phenyl (7), Cyclo(leucyl-proline (8), Cyclo(L-Phe-Pro) (9),7-methyl-1H-purin-6(7H)-one (10), Cyclo(L-Phe-Pro) ( 11),2H-Purin-2-yl,2-amino-1,3,6,9-tetrahydro-6-oxo-9- -D-ribofuranosyl-(12),4-hydrox ybenzoic acid(13), Fumalic acid(14), (S)-2',3'-dihydroxy-1-(1H-indol-3-yl)propan-1-one(15 ), (R)-2',3'-dihydroxy-1-(1 H-indol-3-yl)propan-1-one(16), Benzopyran derivatives(17), 2,4-dihydroxybenzoic acid(19), cyclo[Pro-Val](23),2'-methyl-1H-indole-3-carboxylic acid(24), methyl 4-hydroxybenzoate(25),3-Pyridineethanol(26), methyl 2-hydroxy-3-(1H-indol-3-yl)propanoate(27), cyclo[Gly-Leu](28), N-phenethylacetamide(29), cyclo[Leu-Ala](30), cyclo[Val-Leu](31), cyclo[Tyr-Pro](32), cyclo[Ala-IIe](33), cyclo[Ala-Val](34), cyclo[Trp-Ala](35), cyclo[Trp-Ser](38), cyclo[Trp-Val](39),1,4-Benzenediol (40), cyclo[Trp-Pro](41),1-Butanone,2'-hydroxy-1-(1H-indol-3-yl)-(42),3H-Indole-3-carboxylic acid (43)。
In a word,there were two problem needing to resolved.Firstly,amount of the secondary metabolists that microorganism produced was very little,so it was difficult in screening.Secondly,the range of screening was so limited.In order to search special activities of novel compounds and provide guiding compounds for studies on new medicine, we should take better advantage of mangrove soil microorganism,such as enlarging fermentation scale,optimize culture method to produce secondary metabolists directionally and screen in highly efficient and wide-ranging way.
引文
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